Catalytic dissymmetrization of meso-2-imidazolidinones: Alternative route to chiral synthons for 1,2-diamines

Tetrahedron Letters

Volumn 45, Issue 51, 2004, Pages 9327-9330

  Ishizuka, Tadao ^a   Katahira, Tomokazu ^a   Seo, Ryushi ^a   Matsunaga, Hirofumi ^a   Kunieda, Takehisa ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

Diamine; Imidazolidinone; Synthon

Indexed keywords

2 IMIDAZOLIDINONE DERIVATIVE; BORANE DERIVATIVE; DIAMINE DERIVATIVE; OXAZABOROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; DEACYLATION; ENANTIOMER; ENANTIOSELECTIVITY; REDUCTION;

EID: 8844264547     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.129     Document Type: Article

References (12)

1. P.C. Wang Heterocycles 23 1985 3041 3042
2. For a review, see: L. Denis, G. Thierry Le, and M. Charles Angew. Chem., Int. Ed. 37 1998 2580 2627
3. For examples, see: S. Kobayashi, H. Uchino, Y. Fujishita, I. Shiina, and T. Mukaiyama J. Am. Chem. Soc. 113 1991 4247 4252
4. T. Mukaiyama, N. Iwasawa, R.W. Stevens, and T. Haga Tetrahedron 40 1984 1381 1392 and references cited therein
5. R. Seo, T. Ishizuka, A.A.-M. Abdel-Aziz, and T. Kunieda Tetrahedron Lett. 42 2001 6353 6355
6. T. Ishizuka, K. Kimura, S. Ishibuchi, and T. Kunieda Chem. Pharm. Bull. 38 1990 1717 1718
7. T. Ishizuka, K. Kimura, S. Ishibuchi, and T. Kunieda Chem. Lett. 1992 991 994
8. N. Hashimoto, T. Ishizuka, and T. Kunieda Tetrahedron Lett. 39 1998 6317 6319
9. K. Yokoyama, T. Ishizuka, and T. Kunieda Tetrahedron Lett. 40 1999 6285 6288
10. N-Monodeacetylation of 1,3-diacetyl-4,5-dimethoxy-2-imidazolidinone showed poor results
11. 3, Z = 2. The structure was refined to the R value of 0.037. We are much indebted to the Yoshitomi Research Laboratories, Yoshitomi Pharmaceutical Ind. Ltd (Fukuoka, Japan) for this X-ray crystallographic analysis
12. Compound 3f was readily synthesized via 4,5-dialkoxy-2-imidazolidinone 13 derived from 1,3-diacetyl-2-imidazolone (12) and NBS in the presence of ethylene glycol mono tert-butyl ether